As the summer sunshine slowly fades, it's easy to feel bummed about the days of sweaters and huddling indoors that lie ahead. But instead of lamenting the end of beach season, we're embracing the fresh start that early fall brings—especially for your finances.

To help get your money in tip-top shape for the rest of 2014, our September financial to-dos are focused on everything from rejiggering your retirement savings to prepping for next year's tax bill—plus fun stuff like booking your holiday travel plans.

So boil up some hot apple cider, lace up your best leaf-crunching boots and get ready to tackle your September money tasks with a positive attitude.

Confirm Your Thanksgiving Travel Plans

When it comes to booking travel arrangements, there's pretty much no such thing as too-early a start. In fact, if you're scheduling a flight, the second Tuesday in September is a great time to score a deal. But cooking the turkey? That can wait another two months.

Review Your Credit Report

It's the most wonderful time of the year… to pull a gratis copy of your credit report! To learn how attractive you may look to lenders and check for any potential errors, access your report at Annualcreditreport.com—but remember that each of the three major bureaus gives you just one free copy a year through this service. So if you used TransUnion back in May, you should make sure you pull from either Equifax or Experian this time around. Or take advantage of Credit Karma's recently unveiled program that lets you pull your free credit report weekly.

Pay Your Tax Bill if You're Self-Employed, Own a Small Business or Freelance

Self-employed workers are typically responsible for paying their estimated taxes four times a year, so remember that September 15 is your third-quarter due date. If you don't file and pay each quarter, the IRS can charge you fines and penalties. Plus, while it might seem tedious to do things piecemeal, you'll avoid having to pay an extra-fat tax bill on April 15. Check out LearnVest's guide to doing your taxes as a freelancer or contract worker for more guidance.

Update Your Roth IRA

If you switched to a Roth IRA in 2013, and then lost money, you have until October 15 to "recharacterize." In other words, you have the option to revert to a traditional IRA and recoup the taxes you paid when you had a higher amount, before you change it again to a Roth IRA (after a set period).

Start Planning for Year-End Taxes

You don't need to be self-employed to start thinking about paying your April tax bill. Consider consulting a CPA or another tax professional to ensure that you've been withholding enough from your paychecks and to see if there's anything you can do to lower your burden come April 15. Confused about the rules? Review our start-to-finish checklist on paying your taxes.

LearnVest Planning Services is a registered investment adviser and subsidiary of LearnVest, Inc. that provides financial plans for its clients. LearnVest Planning Services and any third-parties listed, discussed, identified or otherwise appearing herein are separate and unaffiliated and are not responsible for each other's products, services or policies.